Republicans running to replace U.S. Rep. Chip Roy (R-Dripping Springs) have spent weeks brandishing their conservative bonafides across the deep-red Hill County district.
But at a Bexar County Republican Party debate in San Antonio Thursday night, candidates were quizzed on a different challenge they could soon face as the newest member of the city’s congressional delegation: Representing the party’s values in a landscape dominated by Democrats.
Texas’ 21st Congressional District starts near Alamo Heights and stretches northwest past Fredericksburg, making for a deep red seat that gave President Donald Trump more than 60% of its vote in 2024.
While that political lean didn’t change much with redistricting, the new maps did expand the district’s reach into blue Bexar County, where even conservatives agree the role of a Republican official is much different than out in more rural territory.
Earlier that day, many of the county’s GOP leaders and candidates were at a San Antonio City Council meeting lobbying for more coordination between local law enforcement and ICE — a perspective met with boos so loud that Bexar County’s lone Republican commissioner Grant Moody (Pct. 3) could hardly make his comments.
“Fighting over whether they want to support ICE or not — that’s a metropolitan issue,” former Bexar GOP Vice Chair Kyle Sinclair, who is now among the dozen candidates running for the GOP nomination on the March 3 primary ballot, said during the debate later that night.
“It’s hard to go from the Hill Country area to focusing on a metropolitan city and the major issues that you deal with — from the Tren de Aragua gang, to human trafficking, to drug trafficking, to police issues, to crime,” he told the audience of roughly 150 people at Norris Conference Center near the North Star Mall.
The last San Antonian to represent the district was Lamar Smith, a pragmatic Republican attorney who served three decades before retiring amid a changing party makeup in 2018.
Since then the district’s boundaries have been drawn much redder, and Roy would go on to carve a very different reputation, holding fellow Republicans’ feet to the fire on conservative priorities like debt management and border security — occasionally annoying GOP colleagues left to answer for their party’s policies in less conservative territory.
Now Roy is running for Texas Attorney General instead of reelection, and most of the candidates hoping to replace him are following his playbook.
They spent the roughly two-hour debate focused on the shortcomings of a Republican-controlled Congress they argued has failed to rein in spending and do enough to support President Donald Trump’s economic and border policies, with relatively little mention of the Democrats who control zero levers of power at the state and federal levels.
“We have to stop wasting our time on crazy liberals and start talking to our own congressman, our own fellow members in Congress, and say, ‘Why are we voting for bad bills? Why are we voting for runaway spending?'” said Mark Teixeira, a former Major League Baseball player who has become the biggest spender in the race.
The crowded GOP primary is likely to advance to a May 26 runoff between the top two vote-takers, since the winner must have at least 50% of the vote.
Stacked resumes
In a year where both parties operatives say they’ve struggled to recruit candidates, the opening in Roy’s district has drawn a surprising number of contenders with impressive resumes — from successful entrepreneurs, to party leadership experience, to federal appointees in the Trump Administration.
Trey Trainor, for example, is an election attorney from Dripping Springs who served as general counsel to many Texas Republicans. He was also a special assistant to the Secretary of Defense and twice chaired the Federal Election Commission, as well as promoted the idea that Trump actually won the 2020 presidential election.
“Looking at how money is spent in politics, where money is invested in politics and politics, … you’ve got to have transparency in the process,” Trainor told the audience Thursday. “As somebody who’s dealt with the federal campaign finance system, dealt with filing ethics reports and making sure that everybody else in the government gets them done correctly, I’m the right guy to do that.”
Financial analyst Michael Wheeler lived all over the world working for J.P. Morgan, Bank of America and Morgan Stanley before moving to Texas in 2019. He’s since chaired the Kendall County Republican Party and served as Trump’s appointee to the Small Business Administration.
“We talked about a lot of issues tonight, but we can’t deal with immigration, we can’t deal with Greenland, we can’t deal with any of this stuff until we deal with this [national] debt,” Wheeler said at the debate. “Please send somebody to Washington to finally deal with it.”
Software engineer Paul Rojas worked on a team that discovered water on the moon and then built a firearms company that supplies weapons to the U.S. military.
U.S. Navy veteran Jason Cahill was an intelligence asset in Operation Enduring Freedom and Operation Iraqi Freedom, and went on to build his own oil and gas company in Boerne.
Meanwhile Heather Tessmer took her degree from St. Mary’s law school on to build the firm, Tessmer Law Firm, PLLC.,with regional recognition, known for its “Ever argue with a woman?” billboards.
“I can’t believe it when I look at the impressive group of people who stepped up for this office,” Bexar County Republican Party Chair Kris Coons remarked to the crowd on Thursday night.
Yet the candidate who has sucked up most of the oxygen in the race is Teixeira, despite only moving to Texas several years ago and having very little prior involvement in Republican politics.
On Thursday he told the audience he’d been blessed with a successful career in baseball, but that his faith called on him to do something more. He likened his candidacy to Trump’s in that they both had enough money and fame that they didn’t need to run for office — they did so to make a difference.
“[Trump] went to Washington, D.C. as an outsider. He had already been successful. He was already rich and powerful and famous,” Teixeira said. “… I feel like President Trump and I have a lot in common.”
Meanwhile, volunteers opposing Teixeira were approaching attendees on their way out to talk about his recent move to Texas and his lack of Republican voting history — an opposition tactic rarely seen in such rooms.
One even distributed flyers highlighting his past comments about athletes needing to become more vocal about stopping climate change, and connections to a charter school that promoted its DEI policies.
“Replacing Chip Roy with someone who is not who they claim to be is not something that I think that this district will do if we are properly informed,” candidate Daniel Betts, a criminal defense attorney from Dripping Springs, said during the debate.
A focus on San Antonio
Before Republicans’ mid-cycle redistricting effort, Texas’ 21st Congressional District stretched all the way north to Austin.
Under new maps that part is gone, creating a more San Antonio-centric district that’s drawing unusual attention to this area in the final stretch.
“Not having Austin in this district … we really have to focus on what’s going on in San Antonio, because it’s now the major population base in the district,” Trainor said in an interview after the debate.
Indeed, many candidates used their time Thursday to stress their connections to San Antonio as well as their understanding of its political landscape.
Rojas described growing up in a military family on San Antonio’s South Side and going on to receive degrees in physics and software engineering at St. Mary’s University. Tessmer talked about building her law firm here before moving out to the Hill Country when the courts shut down during the Covid-19 pandemic.
Northside businessman Weston Martinez touted an endorsement from former conservative Councilman Clayton Perry (D10), and talked about how his decades of experience with San Antonio’s local policymakers shaped his ability to navigate the ICE discussion at City Hall.
“I went straight up to the city manager to ask him a question … Then I went up to two council members … and then I went up to the city attorney to present the same thing,” Martinez said. “Why? Because I have those relationships.”
Meanwhile Sinclair, who currently lives in U.S. Rep. Tony Gonzales’ (R-San Antonio) district, said the 21st needed someone rooted in Bexar County, and that his background as a hospital executive made him the one with relevant experience to the most pressing issues on Congress’ plate.
“Bexar County covers 17% of District 21,” he said. “People don’t understand, that’s 338,000 constituents.”
Congressional candidates don’t have to reside in the districts they represent, but Sinclair is among a handful of candidates taking heat for that fact.
Teixeira’s home Bee Cave wasn’t in TX21 under the old or new boundaries. Meanwhile Trainor, who was considering running for AG before Roy jumped into that race, was cut out when the Supreme Court OKed the new maps in December.
Multiple candidates sought to call attention to the issue Thursday night by asking for a show of hands on who lives in the district and building it into their responses to the moderator.
“If you are running for this seat and you don’t live in District 21, you are running for yourself,” said Betts. “You’re not running for the people that you should represent.”
Working across the aisle
In a county with far more Democrats than Republicans, Coons has long stressed the challenge of finding candidates who can sell their party’s ideas to a broader audience.
On Thursday night she tossed them questions to test that ability — delivering some mixed results from a group for which the biggest hurdle is still getting through a GOP primary.
Cahill, for example, fielded a question about how he’d talk to people who fear the overturning of Roe v. Wade is killing women with ectopic pregnancies.
“I’d go with Charlie Kirk, he was the biggest advocate of life … and there is [rarely an] instance in which you cannot bring a baby to term,” he said — before adding his experience running a business had taught him to work with people of all beliefs and backgrounds.
Former Boerne Councilman Jacques DuBose got one about collaborating with local officials to deliver for his district, and said that as a Navy veteran and former councilman, he understood how critical it would be to work together on protecting the area’s military installments.
“Being connected, being available, working with those elected officials — it might be challenging in some of the blue cities or where you have a liberal mayor,” he said. “But I would still collaborate and hear them out.”
Meanwhile Wheeler was asked whether the U.S. should separate families during immigration enforcement — something Coons joked was to prepare him for when he’s interviewed by The New York Times.
“If you came into the country illegally, the law is the law,” Wheeler said. “I’m sorry this has happened. You know who started this? Obama. He’s the one that started separating the families, right? But the law is a law, and I’m sorry, this is a human catastrophe.”
Two other Republican candidates, Zeke Enriquez and Peggy McCormick Wardlaw were unable to attend.
Early voting for the primary starts Feb. 17. Find out what congressional district you live in here.
Bexar County residents can download a copy of their personalized sample ballot after checking their voter registration status here.
